Calendar

What’s Happening?

There’s always something to see or do in Highland Park! Check out our calendar to plan your next visit.

 

Featured Events

 

Note: The sponsoring organization for each event is included in the event listing. The City does not sponsor or endorse events listed on the calendar except those attributed to the City of Highland Park. Please direct any questions to the sponsoring organization.

Event Listings

Filtering by: “The Lot”

Stews & Brews (And Blues!)
Nov
2

Stews & Brews (And Blues!)

Stews & Brews (And Blues!)

November 2, 2024 | 5 PM - 9 PM
The Lot | 525 Central Ave.


Hearty comfort foods, refreshing beverages, live blues music, & cozy fire pits… This fan-favorite Midwestern festival returns to Highland Park for a third year.

Cool weather means hearty comfort foods and hot beverages; the City of Highland has the perfect event to warm your body and soul! Stews & Brews returns for a third year to Downtown Highland Park (The Lot, 525 Central Ave., enter at St. Johns and Park Avenues) on November 2 from 5 - 9 PM. Wrap up the City’s 2024 event season with savory stews and delicious brews, while grooving along to live blues music.

  • 5 PM - 6:30 PM: Mississippi Heat, this world-class Chicago-based band brings traditional Mississippi blues sound and culture to kick things off!

  • 7 PM – 9 PM: Chicago blues master, Wayne Baker Brooks, headlines. His liquid fire guitar playing honors his blues heritage for all to enjoy.

Stews & Brews is not your ordinary chili cook-off or craft beer fest. This free, all-ages event offers attendees an array of cold weather comfort foods like chili, pozole, lamb stew, beef stroganoff, Hungarian goulash, potpies, and a variety of soups. Attendees can pair their dish of choice with dozens of unique brews including craft beers, spiced wine, hot toddies, mulled ciders and more!

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Scarecrow Fest & Walk
Oct
19

Scarecrow Fest & Walk

Scarecrow Fest

October 19 | 12 PM - 5 PM
The Lot | 525 Central Ave.

Downtown Highland Park will transform into an autumn wonderland on October 19, complete with two dozen festive scarecrows decorated by local businesses. Start the day with a self-led, leisurely Scarecrow Walk through Downtown Highland Park, where businesses will showcase the spirit of the season with unique decorated scarecrows in front of their stores. Head back to The Lot (525 Central) to cast your vote for “Best in Show Scarecrow” and commemorate the fall season with scarecrow-themed family fun, kids’ activities, live music, food, decorations, and more, including a one-of-a-kind fall-themed photo op with Mermaid Elle.

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Oktoberfest
Sep
28

Oktoberfest

Oktoberfest

Saturday, September 28 | 12 PM – 10 PM
The Lot - 525 Central Ave.



Celebrate fall and all things German with beer, bites, and Bavarian music at the third annual Oktoberfest presented by the City of Highland Park. The fun takes place at The Lot (525 Central) on Saturday, September 28 from 12 PM - 10 PM. Start the day with traditional family-friendly activities, dancing, food, live entertainment, and contests. At 5 PM, switch up the vibe with adult-centered fun and a full headlining band.

Throughout the day and in between sets, Oktoberfest will bring interactive activities and shows to the crowd! The fun begins with the CirquesExperience Wheel Show: the team will roll in with gym and Cyr wheels for a performance you are sure to remember. The show team includes National team member Casey Crowe, bronze medalist at 2022 Cyr Wheel World Championship, and US team member Karly O’Brien.

Guests can also enjoy polka dancing, a beer stein-holding contest, hammer-schlagen, axe throwing, a high striker, ring-o, corn hole, pretzel necklace making, and more!

 

Entertainment Lineup

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Decades
Sep
14

Decades

Decades

We are turning back the clock and bringing the ultimate musical throwback experience to downtown Highland Park with Decades. The Lot’s newest food and music festival will feature fantastic headlining entertainers performing iconic hits from the 70s, 80s, and 90s; bringing together decades of music fans!

Travel back in time to experience the groovy sounds, rad tastes, and cool trends from these three decades through a selection of live performances and food and beverage vendors. An interactive “Decades of Music” trail throughout downtown Highland Park businesses adds an element of adventure to this event. Plus, stick around after sundown for a totally tubular Decades-themed drone show!


Lineup

  • 12:15 PM – 2:15 PM: Decades commences with Chicago-based Four Man Band’s rock and pop covers of iconic sounds from Aerosmith, Police, Queen, and more.

  • 3:00 PM – 4:45 PM: Up next is 7th Heaven, known for their three-time #1 spot on the Midwest Billboard Charts. Their original pop, rock, and dance songs are not to be missed!

  • 5:00 PM: Soul2Sole’s award-winning Phenom all-boys dance team showcases a Decades-inspired routine

  • 5:30 PM - 7:15 PM: Get a groove on with funk and disco tribute band, The Disco Circus! Once this circus takes the stage, the crowd will be transported back to the 7os with hits from the Bee Gees, ABBA, Donna Summer, and more.

  • 8:00 PM: Experience a Highland Park-themed drone shone

  • 8:15 PM – 10:00 PM: Decades will conclude with The 1985; the ultimate 1980s music tribute experience. Performing classics from Journey, Bon Jovi, Madonna, and others, get ready to party like its 1985.

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Vintage Car Show
Aug
11

Vintage Car Show

Vintage Car Show

Peruse a variety of cars ranging from vintage models to unique classics, local Highland Park commercial vehicles, muscle cars, hot rods, and more, dating from 1907 to 1981.

The iconic Batmobile, courtesy of the Klairmont Kollections Automotive Museum, is also back by popular demand. This classic vehicle will create a great photo opportunity for both the young and the young at heart!

Plus, enjoy a live radio broadcast with DJ Eddie “V,” bites, and beverages.

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Bitter Jester Music Festival Finale
Jun
29

Bitter Jester Music Festival Finale

Saturday, June 29, 2 PM - 10 PM

It’s more than a competition, it’s a destination event, complete with music, food, and beverages.12 bands showcase their virtuosity at The Lot, competing for the winner’s title. Many BJMF alumni have gone on to perform on Late Night with Seth Myers, Saturday Night Live, and American Jukebox, as well as at Lollapalooza, Riot Fest, South by Southwest, and Ravinia Festival.

Get more info on the festival here.

*This event is a privately organized festival, hosted by the City of Highland Park

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Taste of Highland Park
Jun
21
to Jun 22

Taste of Highland Park

The City of Highland Park is bringing the ultimate lineup of entertainment and dining to The Lot (525 Central Ave.) with its opening festival, the Taste of Highland Park. Internationally-touring platinum artists Dishwalla and Spin Doctors headline, globally-recognized DJ Madrid returns as The Lot’s resident DJ, and 13 premier food vendors are ready to satisfy every palate!

An unbelievable lineup of nationally-recognized bands will take the stage over the course of two evenings, June 21 & 22, from 5 PM - 10 PM:

FRIDAY, JUNE 21

5 PM - 6:15 PM: The Taste of Highland Park commences with the Chicago-based Jaren Grey Band’s unique brand of heartland rock covers and original songs

• 7 PM - 8 PM: Up next is famed 90s rock band Nine Days, known for their memorable hit “Absolutely (Story of a Girl)”

• 8:30 PM -10 PM: Platinum-selling band Dishwalla, famously known for fan-favorite and Billboard Award “Best Rock Song” of 1996 “Counting Blue Cars,” will wrap up evening one of the Taste

SATURDAY, JUNE 22

• 5 PM - 5:30 PM: Highland Park’s very own Uptown Music Theater opens evening two of the Taste with a Broadway Favorites Concert. Get a sneak peek of their upcoming production of Les Misérables; opening July 2024 and benefitting the Highland Park Community Foundation

• 6 PM - 7:15 PM: Local favorites Serendipity will bring their high-energy, iconic playlist of hits from the 70s, 80s, and today to ignite the crowd

• 8 PM - 10 PM: The Taste of Highland Park will conclude with alternative rock band Spin Doctors, best known for chart-topping hits including “Little Miss Can’t Be Wrong” and the Grammy nominated song “Two Princes”

On-site vendors will bring a wide variety of food and drink including Mexican, Indian, American, Venezuelan, vegan/vegetarian, sweet treats, grilled items, pizza, wine, beer, cocktails, and more. Participating food vendors include Bella Ru Catering, BWB Shakes, Cafe Dacha, Curt’s Café, Indus Progressive Indian Dining, Judy’s Pizza, La Taquiza HP, Lynfred Winery, Michael’s Grill & Salad Bar, Pixca, Ravinia Brewing Company, Sugarcoated, and Tamales. Libations will be available for those 21 and older!

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French Market
Jun
9

French Market

French Market

Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.

Featuring: Art for a Better Life, Bill’s Organic Olive Oil, Coffee Cake Guys, Joanna Beaumont Jewelry, Kitchen Works, Mi Ho Candle Co., Moda’s Boutique, Patisserie Coralie, Six Generations Farm, Solala, Sqwormy Luxury Accessories, Tcreativ Designs, and more!

Live Music by Mark Lyons

The French Market takes place Sundays, June 9 - September 29, 10 AM - 2 PM.

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Stews & Brews
Oct
13

Stews & Brews

This cool weather event will get attendees warmed up with a variety of hardy stick—to-the-ribs stews including chili, jambalaya, Hungarian goulash, chicken pot pie and more. All kinds of brews will be available too, from craft beer, spiced ciders and wines, to hot toddies, hot chocolate and kombucha! A stellar line-up of blues artists will grace the stage as well.

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Bitter Jester Music Festival Grand Finale Concert
Jun
25

Bitter Jester Music Festival Grand Finale Concert

The Midwest's largest professional "battle-of-the-bands" style concert and competition series will feature bands and solo performers that 101.9 The Mix calls "Future Headliners!" and will be announced after the summer-long Festival culminates as part of the Taste of Highland Park weekend. The Grand Finale Concert will feature a wide variety of food and drinks vendors all day long as well as a dozen musical acts TBD from multiple states. 

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Taste of Highland Park
Jun
24

Taste of Highland Park

This fan favorite at The Lot will showcase a variety of delicious cuisines and beverages. A fantastic weekend lineup of live music will include nationally recognized headliners and on-site fun for the entire family.


Friday will kick-off with a set by former resident DJ for Virgin Megastore Chicago, DJ Madrid, who will also spinning all night long in between sets performed by a cappella’s favorite boy band, Radius Vocals, and the nation’s #1 Yacht Rock band, Yachtley Crew. Saturday boasts the following acts including: the jam band ensemble of Marcus Rezak Band featuring Shred is Dead and Gumbo, roots singer/songwriter Joseph Huber, Grammy nominated bluegrass musicians Sister Sadie Band, The Complete Beatles Tribute Band American English, and Chicago’s own rock band The Ides of March powered by Grammy winner Jim Peterik.

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Taste of Highland Park
Jun
23

Taste of Highland Park

This fan favorite at The Lot will showcase a variety of delicious cuisines and beverages. A fantastic weekend lineup of live music will include nationally recognized headliners and on-site fun for the entire family.


Friday will kick-off with a set by former resident DJ for Virgin Megastore Chicago, DJ Madrid, who will also spinning all night long in between sets performed by a cappella’s favorite boy band, Radius Vocals, and the nation’s #1 Yacht Rock band, Yachtley Crew. Saturday boasts the following acts including: the jam band ensemble of Marcus Rezak Band featuring Shred is Dead and Gumbo, roots singer/songwriter Joseph Huber, Grammy nominated bluegrass musicians Sister Sadie Band, The Complete Beatles Tribute Band American English, and Chicago’s own rock band The Ides of March powered by Grammy winner Jim Peterik.

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Takeout Tuesday: Finale!
Aug
30

Takeout Tuesday: Finale!

Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?

August 30: Finale!

We’ll be saying good-bye to our Take-Out Tuesday season fondly with special offerings throughout!

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Takeout Tuesday: Local Performance Showcase
Aug
23

Takeout Tuesday: Local Performance Showcase

Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?

August 23: Local Performance Showcase

Some of the area's finest musical and entertainment acts will be onsite to wow attendees in this encouraging showcase to support all performers.

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Takeout Tuesday: Fashion Night
Aug
16

Takeout Tuesday: Fashion Night

Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?

August 16: Fashion Night

In time for back to school fashions, we’ll have retailers onsite to show off the latest trends!

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Takeout Tuesday: Home Refresh Night
Aug
9

Takeout Tuesday: Home Refresh Night

Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?

August 9: Home Refresh Night

We have a plethora of beautiful home decor establishments, landscape companies, interior designers and more in Highland Park. Come out to see what small (and big!) changes you can make to beautify your home.

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Takeout Tuesday: Party Planning Night
Aug
2

Takeout Tuesday: Party Planning Night

Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?

August 2: Party Planning Night

Want to support local businesses when planning your next party? We’ll have Downtown HP businesses onsite to make your lives easier!

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